Halocarbon Chemistry. 2. Use of the 1,1-Difluoro-2,2-dichloroethyl Group for Phenol Protection. Regulation of Ionization during the Torgov Steroid Synthesis

S. G. Will; P. Magriotis; E. R. Marinelli; J. Dolan; Francis Johnson

doi:10.1021/jo00225a101

Halocarbon Chemistry. 2. Use of the 1,1-Difluoro-2,2-dichloroethyl Group for Phenol Protection. Regulation of Ionization during the Torgov Steroid Synthesis

S. G. Will
, P. Magriotis
, E. R. Marinelli
, J. Dolan
, Francis Johnson

Pharmacological Sciences

Stony Brook University

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

Abstract

The use of the easily cleavable (dilute base) HCl₂CCF₂O in place of CH₃O in the Torgov steroid intermediate completely inhibits solvolysis of the tertiary alcohol during acetylation and the derived acetate, via a (π-allyl)Pd complex, is extremely useful for the previously difficult alkylation of cyclic β-keto esters that are precursors of ring D in steroids.

Original language	English
Pages (from-to)	5432-5433
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	50
Issue number	25
DOIs	https://doi.org/10.1021/jo00225a101
State	Published - Dec 1985

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title = "Halocarbon Chemistry. 2. Use of the 1,1-Difluoro-2,2-dichloroethyl Group for Phenol Protection. Regulation of Ionization during the Torgov Steroid Synthesis",

abstract = "The use of the easily cleavable (dilute base) HCl2CCF2O in place of CH3O in the Torgov steroid intermediate completely inhibits solvolysis of the tertiary alcohol during acetylation and the derived acetate, via a (π-allyl)Pd complex, is extremely useful for the previously difficult alkylation of cyclic β-keto esters that are precursors of ring D in steroids.",

author = "Will, \{S. G.\} and P. Magriotis and Marinelli, \{E. R.\} and J. Dolan and Francis Johnson",

year = "1985",

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journal = "Journal of Organic Chemistry",

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AU - Will, S. G.

AU - Magriotis, P.

AU - Marinelli, E. R.

AU - Dolan, J.

AU - Johnson, Francis

PY - 1985/12

Y1 - 1985/12

N2 - The use of the easily cleavable (dilute base) HCl2CCF2O in place of CH3O in the Torgov steroid intermediate completely inhibits solvolysis of the tertiary alcohol during acetylation and the derived acetate, via a (π-allyl)Pd complex, is extremely useful for the previously difficult alkylation of cyclic β-keto esters that are precursors of ring D in steroids.

AB - The use of the easily cleavable (dilute base) HCl2CCF2O in place of CH3O in the Torgov steroid intermediate completely inhibits solvolysis of the tertiary alcohol during acetylation and the derived acetate, via a (π-allyl)Pd complex, is extremely useful for the previously difficult alkylation of cyclic β-keto esters that are precursors of ring D in steroids.

UR - https://www.scopus.com/pages/publications/33845378789

U2 - 10.1021/jo00225a101

DO - 10.1021/jo00225a101

M3 - Article

AN - SCOPUS:33845378789

SN - 0022-3263

VL - 50

SP - 5432

EP - 5433

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JF - Journal of Organic Chemistry

IS - 25

ER -

Halocarbon Chemistry. 2. Use of the 1,1-Difluoro-2,2-dichloroethyl Group for Phenol Protection. Regulation of Ionization during the Torgov Steroid Synthesis

Abstract

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